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<h1><a href="https://archiveofourown.org/works/26989810">Time For A Lesson</a> by <a class='authorlink' href='https://archiveofourown.org/users/raths_kitten/pseuds/raths_kitten'>raths_kitten</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Beads, Anal Plug, BDSM Switch Jimmy Novak (Supernatural), Bottom Dean Winchester, Dom Castiel/Sub Dean Winchester, Double Anal Penetration, Established Relationship, M/M, Punishment, Sex Toys, Spanking, Team Dean Winchester's Red Ass</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-13</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-13</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 23:21:06</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>7,168</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/26989810</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/raths_kitten/pseuds/raths_kitten</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Dean and Jimmy interrupt Castiel’s Zoom lesson and get punished for it.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester, Castiel/Jimmy Novak/Dean Winchester</td></tr>

<tr><td><b>Comments:</b></td><td>7</td></tr>

<tr><td><b>Kudos:</b></td><td>146</td></tr>

<tr><td><b>Collections:</b></td><td>DCJ Hiatus Indulgence 2020</td></tr>

</table>

<a name="section0001"><h2>Time For A Lesson</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Written for the <a href="http://dcjbigbang.tumblr.com">Dean/Cas/Jimmy Hiatus Indulgence</a>: Covid Edition. (Covid is the reason why they’re all at home, but I don’t really mention it. Nobody gets sick! And before you gets too excited, the dp is not with Jimmy, because Castiel can be mean like that.)</p><p>I got the general idea from a friend who suggested Dean interrupting professor Cas with the naked challenge. This is not that, but it’s for you anyway. ;)</p><p>Thanks a lot to <a href="https://archiveofourown.org/users/captainhaterade">captainhaterade</a> for beta reading!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Castiel turned on his laptop and made a cup of tea while it was starting up. It was an old thing, and he didn’t like looking at it too closely during the booting process because as soon as something took a little longer than usual, he started to worry. At least Jimmy wasn’t here right now to laugh at him.</p><p>With his mug of tea by his side, he shuffled his notes and spread out the few papers he had, really missing access to his office printer. But the university was closed to the students and it would be imprudent of him to risk a trip over there. At least he was saving some trees.</p><p>A glance at his watch showed that it was almost time, so he straightened his tie and logged into Zoom. He’d given up on a jacket because he was at home, after all. But that was as far as he was willing to go, even if his students teased him about it. He was still their professor and this was still an official class. Virtual or not, there was decorum to uphold.</p><p>As soon as he’d opened the remote classroom, he could hear his students join. There were still five minutes to go and he smiled at their eagerness. They were good kids. He waved, his microphone still off, and watched them wave back and otherwise interact with each other, probably through private chats going by some of their faces, until it was officially time for his lecture to start.</p><p>He took a sip of his tea and unmuted his microphone. “Welcome to another remote Applied Ethics class. The good news is still that this whole fiasco should give you a lot of fodder for your upcoming theses.” He got a few chuckles in reply and smiled. Alright. Good start.</p><p>“Today we will talk about how the allegory of the cave still holds up, and how it can be applied to modern media and the emergence of so-called ‘alternative theories’.” He made air quotes around the words and smirked when he saw some of their faces light up. It would be a great topic for a whole thesis and he hoped someone would bite.</p><p>“Who can sum up the allegory for us?” Castiel saw several actual hands as well as virtual hands go up. He opened his mouth to call out a name when suddenly the door to their bedroom opened and he was momentarily distracted. Usually Jimmy and Dean stayed out of his hair when he held his lessons, but now they joined him in the living room.</p><p>Castiel raised his eyebrow at them but then focused back on the screen. “Ok, Emma. Please enlighten us.”</p><p>When she started, Castiel looked up at his two roommates again. Jimmy was generally slacking off working remotely, but since he always crammed in his assignments just on time, he fared ok. Dean, less so. He was a mechanic, but his garage had temporarily closed and sent him home without pay. Neither Cas nor Jimmy gave him any grief for it, but Cas knew it was weighing heavily on him. Dean already felt like he wasn’t providing enough, and this was a huge setback. But since they all lived together and shared expenses, they were still doing fine.</p><p>Right now, though, there was a dangerous glint in both of their eyes and as soon as they realized Castiel’s attention was on them, they embraced each other in a passionate kiss. Shocked, Castiel stared at them, only realizing he’d zoned out on Emma once it was too late.</p><p>Shit. He focused back on the screen. “Anyone want to add to that?” A few hands raised, thank fuck, and Castiel picked Kevin. As soon as the kid started, Dean’s shirt was flying past him, just off-screen, and he was forced to look up.</p><p>Jimmy had Dean stretched out for Cas to admire and was playing with Dean’s nipples, causing Dean to bite his lips, hard, in an attempt not to make any noises. Fuck. Dean’s nipples were <i>really</i> sensitive. But he was a good boy and could keep quiet. Castiel was a little more concerned about Jimmy. And his own sanity.</p><p>Making sure his arm was off-camera, he flipped them off and focused back on his lecture. He heard Jimmy’s snort and knew he’d be in for one hell of a session. But so would Dean and Jimmy, as soon as he was able to get to them.</p><p>He really tried to focus on Kevin, but it was hard. Thankfully, he knew his kids well enough, by now, and Kevin was thorough. Once he’d stopped talking, Castiel nodded. “Thank you both. Now, how does it still hold up? Have we evolved beyond the shadows? Do we still kill the messenger? Thoughts?”</p><p>Cas had meant to slowly lead them on, one part of the allegory at a time, but a quick glance up confirmed that Dean and Jimmy were still going at it, and he knew he wouldn‘t be able to concentrate well enough. Dammit. They should know better than to mess with his lessons.</p><p>He picked David to start the discussion and was hit by Dean’s pants which had been kicked at him under the table. Biting off a growl, he couldn‘t help but glare at them. Which was a mistake, because it meant he was <i>looking</i>. And Dean wasn‘t wearing any underwear. The second they realized he was paying attention again, Dean turned around and showed off the plug he was wearing, wiggling his ass enticingly. And they‘d pay for this, the both of them.</p><p>Castiel bit his lip and quickly reached for his tea, breathing in the scent to try and calm himself down. Focusing back on the screen, he realized Amy had raised her hand and bless his students, really. “Yes, Amy. Go on.”</p><p>He tried to pay attention to his students with all of his focus, but Dean muffled a grunt and he had to look. Jimmy had him spread out on the table now, so Castiel had a better view of him playing with the plug, thrusting it in and out in no particular rhythm, keeping Dean on his toes, quite literally. Castiel hid behind his mug once more and watched them until he realized the background noise coming from the screen had stopped.</p><p>“Thank you, Amy. Anyone else? Yes, Kevin?” Castiel could hear a bottle of lube being uncapped and for a second he stared at his screen, sure the others must have heard. But nobody seemed bothered, so the sound probably only felt extremely loud to him.</p><p>He should have had more restraint than to look again, but it was compulsory. Jimmy had pushed two fingers in alongside the plug, and Dean was biting his lips bloody trying to keep the noises in. He really was such a good boy. Jimmy, on the other hand, was a little shit. Castiel surreptitiously moved in his chair and adjusted his pants, very happy for the crappy, close angle of his laptop’s camera.</p><p>“Professor Novak? Are you ok?” One of his students asked, and Castiel couldn’t even tell which of them it had been. He focused back on the camera and found twelve pairs of eyes staring at where he was probably showing up on their screens. At least nobody was looking directly into the camera and thus right at him. He swallowed.</p><p>“Yeah, it’s just…” He looked up at a loss and spotted Jimmy trying to stifle his laughter with both hands, Dean forgotten on the table, and that was just… He saw red and got up, grabbing Jimmy by the collar of his shirt—other hand clamped firmly over his brother’s mouth so he’d keep quiet—and dragged him into the bedroom.</p><p>He pushed Jimmy inside and when he was sure he was inaudible to his students, he hissed, “Go in the corner and think about what you’ve done. Don’t move. Don’t touch yourself. Or I will know.”</p><p>“How will…” Jimmy started, but Castiel had already slammed the door shut. When he got back, Dean was standing next to the table, head down and arms crossed in front of himself, looking contrite. His very good boy.</p><p>Castiel sighed and stopped, cupping Dean’s cheek and giving him a quick kiss. “Kneel,” he whispered in his ear and ruffled his hair affectionately. As soon as he’d stepped away to get in front of the screen again, Dean sank down gracefully and inaudibly, hands behind his back, looking at Castiel for approval. When Castiel smiled and nodded, Dean smiled back and then averted his gaze, looking down.</p><p>After he’d settled in front of his screen again, his students’ eyes were even wider. Shit. “I’m sorry.” Castiel started. “It’s just…” Shit, shit shit. “I got… a new cat. And it was distracting. So I locked it in the bedroom. This will not happen again.”</p><p>Apparently that was the wrong thing to say because his students exploded into a chorus of questions about the cat—how old, what breed, what color, what’s their name—and quickly turned into demands to <i>see</i> the cat. Cas gulped.</p><p>He held up a hand to silence them. “I’ll make you a deal. You write essays on today’s topic and if they’re good enough, next week I’ll show you the cat.”</p><p>His students were absolutely delighted and immediately shared their ideas on what aspect they were putting their individual focus on, asking a few specifics like page count and was there a minimum number of citations needed. Since he really just wanted to see what they could come up with on their own, he gave them free range, for once. Also, he felt really bad for the botched lesson. Cas usually prided himself on his professionalism and this was unacceptable.</p><p>A quick glance at Dean found him serenely smiling, gaze still averted, but Castiel could tell he’d been listening in. Because when he ended his lesson a little early, Amy had wished him ‘fun playing with his cat.’ And as soon as the sounds of his students exiting the room could be heard, Dean started meowing.</p><p>Cas snorted and closed his laptop. “Cute.” Dean looked up at him with a smirk and Castiel chuckled, shaking his head. So much trouble, the both of them. “Alright, come here,” Cas crooked his finger. “Crawl.”</p><p>Dean did as instructed, nuzzling Castiel’s thighs and pushing in between his legs. When Cas opened his zipper, Dean looked up at him. “What about Jimmy?”</p><p>“Jimmy can stand in his corner a little longer,” Castiel replied, unbothered, and freed his cock just enough for him to guide it between Dean‘s plush lips. Dean immediately took him deep and started sucking, his hands clasped at his back again without Cas even giving him a command. He raked his fingers over Dean‘s scalp and scratched at his neck in a reward, leaning back and enjoying it.</p><p>A part of him wished he could keep Dean down here for his next lesson and use him as a cockwarmer. But he knew he‘d be punishing himself with that most of all, because he‘d once again be too distracted to focus on his poor students, even if he had no doubt Dean would stay perfectly still. Just having him near was distracting; even after all the time they‘d been together, Dean was a shining beacon demanding his attention.</p><p>And speaking of attention... Cas tugged at Dean’s hair a little more harshly. “Look at me,” he commanded, pleased when Dean’s eyes flew to his. His pupils were blown, his lips stretched wide around Castiel’s cock, but he blinked a few stray tears out of his eyes and focused on Cas as commanded. It was really his look of pure devotion that was the last straw for Cas, and he kept Dean’s head in place before spilling deep down his throat.</p><p>Satisfied for now, Castiel stroked his fingers up and down Dean’s throat to help him come back down and as soon as he could breathe normally again, Castiel pulled him up for a kiss. He could still taste himself and it made him lick into Dean’s mouth until nothing was left.</p><p>Cas reached down to grab Dean’s cock and with the way his boy hissed, Dean must be pretty close himself. But he’d kept his own hands off, because he knew better than that. With a smile, Castiel withdrew from the kiss and pumped Dean’s cock a few times before pulling away. Dean let out a whine, but he didn’t complain.</p><p>“We both know you’re not coming any time soon, after that stunt you pulled today,” Castiel remarked and a mischievous grin flashed over Dean’s face before he caught himself and put on his innocent, apologetic mask again. Cas raised his eyebrow and tugged Dean’s head back.</p><p>He knew neither Dean nor Jimmy actively wanted to sabotage his career, but he had to be strict and make sure this wouldn’t repeat itself. Though he had a feeling Dean had just wanted to be punished in the first place. He wasn’t dumb. He knew Cas wouldn’t thank them, but he should’ve found another way to rile Cas up. They would have to have a talk tomorrow. Today was for corporal punishment, though.</p><p>Or touch deprivation, in Jimmy’s case. He wouldn’t learn, otherwise. With a sigh, Castiel stood up and offered Dean a hand. He’d spent enough time on his knees on the hard floor. Time to put him on the bed. “Let’s join Jimmy before he cracks and earns even more punishment.”</p><p>“I’m surprised he’s still in the bedroom. You didn’t have time to tie him up, did you?” Dean asked, having interlaced his fingers with Castiel’s after he’d gotten up.</p><p>“No. But by now, he knows when I’m really angry,” Castiel explained. He saw Dean flinch and brought their joined hands to his lips and kissed his knuckles, letting Dean know that they were ok. He’d get punished, sure, but that didn’t change a thing about their relationship.</p><p>After coaxing a small smile back on Dean’s face, Castiel guided Dean to their shared bedroom. Jimmy had his own room, mostly for the sake of visitors. And whenever one of them needed alone time, they used it. Most nights they spent together in a big pile in the master bedroom, though.</p><p>Jimmy was still standing in the corner, facing the wall. His posture was relaxed and he was a far cry from being as obedient as Dean, but Castiel was nevertheless impressed. “Alright, Jimmy, you can join us.” His brother’s face lit up as he turned and walked over. But before he could touch, Castiel held up his hand. “But here are the rules. I know what you were trying to prepare Dean for, and you can definitely forget about that tonight. Your dick will not go anywhere near him. And neither will the rest of your body. You’re just here to assist me and watch, ok?”</p><p>Jimmy’s lip trembled but he nodded. Dean looked equally disappointed. Castiel rolled his eyes. “Don’t worry, Dean. You’re still gonna get filled.” Dean perked up. “Get your cute butt on the bed and present.”</p><p>Dean did as instructed and Castiel rewarded him with a few strokes over his hips and ass. Then he lightly tapped the plug he was still wearing. “You ok, baby? A little dry?” Cas asked.</p><p>Dean bit his lip and looked over his shoulder. Castiel knew he wanted to lie, but instead he nodded. “A little, yeah.” </p><p>Castiel nodded and petted him again. “Good boy. That’s what I thought.” No reason for him to suffer unnecessarily. “Jimmy, get me more lube.”</p><p>Jimmy quickly fetched him a bottle and when Castiel held out his hand, squeezed some on his fingers. Not bothering to warm it up first, Castiel spread a liberal amount around Dean’s pucker until he could easily move the plug. He pulled it out and threw it on the bed, then worked more lube inside of Dean.</p><p>“Alright, Jimmy. You can get undressed now, as well,” Castiel commanded before he leaned closer to Dean. “You know, Dean, I don’t think you should suffer for what was essentially Jimmy’s mistake. Do you?” He asked, locking eyes with Jimmy, who was in the middle of taking off his pants. He opened his mouth to protest, but then thought better of it and silently kept undressing. He was learning. Good.</p><p>“Wh.. whatever you think, Sir,” Dean eventually replied and Castiel grinned at Jimmy, conveying that this was what a good boy should sound like.</p><p>“I always enjoy seeing you stuffed full, baby.” Castiel gave his ass a playful slap, which made Dean arch his back in a more pronounced curve. “Jimmy, fetch me the beads. The purple ones.”</p><p>Dean looked over his shoulder, eyes wide. “Thank you, Sir.”</p><p>“You can thank me when we’re done.” Castiel smirked and took off his tie. He loosened the top buttons on his shirt and rolled up his sleeves. The purple beads were their biggest. Castiel usually brought them out when they were preparing Dean for the both of them. But since Jimmy had lost that privilege for tonight, Castiel had to get creative.</p><p>After Jimmy delivered, carrying them reverently and looking very sorry already, Castiel gleefully added a liberal amount of lube straight to Dean’s hole and then started pushing them in one by one.</p><p>A glance at Jimmy revealed him looking anywhere but at Dean and this wouldn’t do. “Jimmy! Don’t think I’m neglecting you. This show is for the both of us. I don’t think you can see well from where you’re standing. Why don’t you go kneel on the bed beside Dean. But face him, so you can fully appreciate what our boy is capable of.” </p><p>Jimmy looked panicked but he nodded. He still hesitated to physically comply, though. “Can I… may I…?” he tried.</p><p>“What, Jimmy?” Castiel smiled. He had a pretty good idea what Jimmy’s problem was. Castiel was thankfully faring better, but only because he’d already gotten off before they started.</p><p>“A cockring. Please?” Jimmy wrung his hands. “I want… to be… good for you, Cas,” he ground out, and oh, how much that must have cost him to say. Castiel gloated. This was almost worth the trouble they put him through. But not quite.</p><p>He nodded. “Alright, go get one. Thank you for telling me how to help you be good.” Castiel winked for good measure, and he knew Jimmy must be seething inside.</p><p>“Thanks, Cas.” Jimmy quickly scrambled off to get a cockring for himself.</p><p>“You don’t need one, baby, do you?” Castiel asked Dean, loud enough that Jimmy could hear him from the other side of the room. “You’re my perfect boy.”</p><p>Dean preened and shook his head. “No, Sir. Thank you for asking, Sir.” The way Dean tacked on the title—with just that little extra spunk—was also meant for Jimmy, Castiel could tell. They’d tried, but Jimmy had flat-out refused to call his brother by anything but his name when they were scening, which Cas and Dean were both okay with. It helped keep a clear distinction between his relationship to Dean and his relationship to Jimmy.</p><p>Jimmy came back and knelt on the bed as instructed, eyes on Dean’s ass, where Castiel had kept playing with the first three beads, pushing them in and pulling them back out again. Now that his audience was back, Castiel worked on adding more.</p><p>Dean had been thoroughly prepped, so he was taking them easily enough. Castiel suspected they had started playing in the bedroom before joining him for his Zoom lecture. But nevertheless, Dean was shaking by the time they’d reached the fifth bead, fists clenched in the sheets.</p><p>The sixth bead took a little more effort. Castiel threw the lube at Jimmy and made him squeeze more at Dean’s pucker. But he wasn’t allowed to rub it in; that was a privilege reserved for Castiel. Jimmy looked equal parts enraptured and miserable.</p><p>Castiel watched the sixth bead pop back out on its own and then pushed it back in a few times before adding number seven. After he’d worked it in, he pressed his thumb on it to keep it in place and took a short break, stroking Dean’s flank. “Good?” he asked.</p><p>Dean let out a loud moan but nodded, head buried in the pillow. Castiel smiled. He let go and tugged the string so the last three beads popped free in quick succession. Dean keened and clawed at the sheets, almost breaking position, but he quickly caught himself again. Castiel pushed them back in, one after the other, before repeating the whole sequence twice more.</p><p>Dean was a shivering mess. Castiel knew how hard it must be for him to hold in his orgasm by now. After all, he also hadn’t gotten to come, yet. But he didn’t plead and beg for it, he just moaned and sobbed prettily into the pillow, knowing Castiel would provide when he felt it was time.</p><p>“You’re doing so well, baby.” Castiel praised him. “So good for me.”</p><p>Dean clenched his ass around the beads in reply, making it even harder on himself. It earned him a kiss to each of his ass cheeks. Castiel focused on Jimmy and found his gaze glued to Dean, just as instructed. His eyes were glassy and he, too, was fisting the sheets.</p><p>Castiel stood back up and pushed the beads back in as far as they would go. Then he reached for the discarded plug, thankful that it was one of their smaller sizes, and used it to plug Dean up and keep the beads inside, mindful to keep the string outside.</p><p>“Oh, fuck,” Dean cursed, probably knowing where this was headed. Even Jimmy finally tore his eyes away and gaped at Castiel.</p><p>“Didn’t think this was all a reward for you, did you?” Castiel explained jovially. “After all, you were complicit.” He nodded his head at Jimmy and his brother scrambled off the bed. “Go fetch me a paddle. I think thirty should be enough.”</p><p>Dean winced, but turned his head. “Yes, Sir. Thank you, Sir.”</p><p>Castiel nodded and spanked Dean a few times with his bare hand in preparation for what was to come. It wasn’t so much about the pain, but it would jostle the beads and that should make it extremely hard for Dean not to come. If his body gave in, Castiel wouldn’t even punish him further. He knew Dean would do his best to stay strong, but that’s not something either Dean or Jimmy needed to know.</p><p>Jimmy came back with the paddle and Castiel didn’t have him kneel back on the bed but stand next to him for the next part. He did the first ten strokes in rapid succession, five on each cheek. Then he took a break and walked around the bed to see Dean’s eyes.</p><p>“You ok?” he asked. Dean looked up at him through tears, but he nodded. Castiel hadn’t hit him very hard, so he wasn’t too worried about hurting him. But he still had to check. “We didn’t properly begin anything yet, but you do know that you can always safeword out, right?”</p><p>Dean raised an eyebrow and wiped a hand over his face, trying to compose himself. “Cas,” he started. “I know that. I’m fine.” Dean smiled. “I love you for checking.”</p><p>“I love you unconditionally,” Castiel replied, crawling half-on the bed so he could give Dean a soft kiss. Then he pulled back. “Remember that for the next twenty.” He winked and Dean groaned, burying his face back in the pillow.</p><p>When he was back in his previous spot, Jimmy cocked his head. “Do you love <i>me</i> unconditionally?”</p><p>Castiel gave him a quick whack with the paddle. “Don’t ruin the moment, Jimmy.” He smirked, though. Of course he did. But… It was different with Dean. And Jimmy knew that, too, the fucker. Jimmy grinned back at him and stuck out his tongue until Castiel whacked him again, a little harder.</p><p>“Ow, fuck.” Jimmy danced away. “You suck.”</p><p>Castiel raised his eyebrow. “I might have, if you hadn’t fucked up my lesson.”</p><p>Jimmy rolled his eyes but took up vigil next to him again. Castiel shook out his arm and focused back on Dean, aiming the next slap right on the plug. Dean yelped and Castiel didn’t give him too much time to breathe but steadily delivered the next nine whacks with the same intensity. He wasn’t as fast as he had been before, though, pausing just enough for Dean to almost relax before he struck again.</p><p>His next series done, Dean was breathing raggedly, not lifting his head from the pillow. “Still ok, baby?” Castiel asked.</p><p>Dean mumbled something incoherently into his pillow. It might have been curses aimed at Castiel or just general complaints, but his safeword was definitely not uttered. “If you hold out for the next ten, I promise you’ll get to come. And then I’ll fuck you, and you get to come again.”</p><p>Perking up at that, Dean straightened his position a little, wiggling his ass to signal he was ready. </p><p>For his next ten strokes, Castiel alternated his aim, the intensity, and the speed—hitting Dean twice in a row, then pausing long enough for him to almost relax, then one more, then a shorter break, then back to two in rapid succession—never giving Dean time to fully prepare or know what was coming next. It might have been a few more than ten, if Cas was honest, but neither of them counted. Or if Dean had, he didn’t complain.</p><p>By the time he was done and dropped the paddle, Castiel himself was panting harshly, as well. He finished unbuttoning his shirt and took it off. Glad he was wearing slacks and boxers, he brushed a hand lightly across his own cock, just to tease himself. Dean first; he’d promised, and Dean deserved it. “You did so good, baby,” Cas praised. “So very, very good for me, Dean.”</p><p>Castiel knelt down on the bed where Jimmy had been before and stroked and petted Dean until his shivers had subsided a little bit. “Shh, shh, baby. I’ll give you your reward, just as promised. You earned it. So good to me.”</p><p>Dean just mumbled incoherently again, this time more thanks than curses audible. With a smile, Castiel got back up and took out the plug, keeping his other hand on the beads to make sure they still stayed in. “Ok, Dean, whenever you’re ready.”</p><p>Dean let out a long, pained keen, which Castiel translated to, ‘I’ve been ready for the past ten minutes.’ He reached around with his free hand to touch Dean’s cock, stroking it once, just when he let go of the beads. Gripping the string, instead, Cas pulled them all out in one smooth motion.</p><p>Dean came immediately, crying out, legs giving out on him. Castiel stroked him through it while Dean rutted against his hand and the bedsheets, still spurting a few drops. When he was done, Castiel crawled back up on the bed, blanketing him, pressing kisses to his neck and hair. Dean was still moving his hips and Castiel couldn’t help but thrust against him, the friction against his cock delicious. This wasn’t part of the plan, though, and punishment for Jimmy wasn’t over yet. But he indulged for a few more minutes.</p><p>“You did so good for me, Dean.” Castiel nuzzled him, their hands interlaced with Dean’s arms stretched out in front of him. “You held out, just like I asked. You were such a good boy for me.” He kissed his cheek. “I love you so much.”</p><p>Dean turned his head, blinking at him sleepily. “Love you, too, Cas.”</p><p>Castiel smiled and kissed him softly, then let go of one hand so he could ruffle Dean’s hair instead. “Remember what I promised you? Are you good or are you out?”</p><p>Dean perked up, trying to get his boneless body to move. But Castiel was still blanketing him. “‘M good,” he replied.</p><p>“You sure?” Castiel asked, nuzzling him again.</p><p>Dean huffed. “Get up and fuck me already.” He moved his head to bump into Castiel’s. “Please, Sir,” he tacked on.</p><p>Castiel chuckled and after one last kiss to Dean’s neck, slid down and rolled off the bed so he could get behind Dean again. This was still a show for Jimmy, who was waiting at the end of the bed with a raised eyebrow.</p><p>“Sometimes I hate you guys so much,” Jimmy complained.</p><p>“You could be snuggling with us right now, but instead you decided to interrupt my lesson.” Castiel shrugged and opened the buttons of his slacks, reaching inside to finally free his aching cock. “And I know you were gonna prepare Dean for the both of us.” He waited for Dean to get into a better position before he reached out to spread his cheeks. “And look at how open our boy is, Jimmy. So ready to take the both of us.”</p><p>Castiel used two fingers to spread Dean and show off for Jimmy, but at the same time he was also assessing if he needed more lube. He glanced at Jimmy. “But just because you’re being punished doesn’t mean Dean and I have to abstain.”</p><p>Jimmy perked up. “Yes. Just use me. The cockring stays on.”</p><p>“Cute.” Castiel reached for the lube. “I told you your cock wasn’t going anywhere near Dean today and I meant it. But go and fetch me a vibrator. The purple one.” It wasn’t too big and Dean would be fine, so they could actually have their scene in a few days. If Jimmy had earned it by then.</p><p>Jimmy closed his eyes and took a deep breath, clearly biting back his reply and counting to ten in his head. Castiel was a little proud of him. He’d only had all of their lives to learn that tantrums would not make Cas cave. But he still forgot. Often.</p><p>When Jimmy turned to go to their toy chest, Castiel leaned forward to be closer to Dean. “You still good, baby?”</p><p>Dean rubbed his cheek against the bedsheet and bowed his back like a cat. Castiel had a feeling he’d be purring, too, if Castiel stroked him just right. “Yesss,” Dean moaned. “Just hurry. I still feel empty,” he sighed. “Don’t make me come empty again.”</p><p>“Promise.” Cas straightened up and added more lube before he finally allowed himself to sink into Dean—while looking straight at Jimmy, who had returned. It was a struggle not to close his eyes, because no matter how stretched out Dean was, or how many times they did this, it always felt wonderful.</p><p>He relished being connected to Dean for a few more breaths before he started a few shallow thrusts. Dean, as exhausted as he must be, was pushing back, demanding more already. Not wanting to drag this out too much, Castiel added a finger on his next thrust. It slid in easily, the anal beads really having done their job, and after a few more thrusts, Castiel added a second finger.</p><p>He kept it up until he could add a third and Dean was crying out into the sheets. Castiel tried to keep his eyes on Jimmy, but it was hard. He’d much rather just focus on Dean. “Are you getting a good show, Jimmy? Can you see how open Dean is? How much he can take?”</p><p>Jimmy whimpered, biting his lip. “Cas, please. I promise to be good. I’ll never disturb your lessons again. I <i>promise</i>.”</p><p>“I believe you,” Castiel replied, then held out his free hand. “Now be good and give me the toy.”</p><p>Jimmy looked a second away from throwing it down and murdering Cas, but he complied anyway. Castiel smiled and stilled, taking out his fingers and carefully inserting the vibrator alongside his cock. He hissed when he realized how cold it was. Next time he’d definitely find a way to warm it up, even if he was just using it on Dean. But it helped to stave off his own impending orgasm, and Dean didn’t seem to complain, either.</p><p>Instead, Dean wailed into the sheets and thrust back, helplessly trying to urge Cas to move again. Castiel placed a comforting hand on Dean’s hip, grounding himself in the process, and then slowly started to thrust out with his cock and in with the vibrator.</p><p>Once he had found a good rhythm, Castiel turned it on to a low setting and cursed, “Fuck, that feels good.” He looked at Jimmy and he wasn’t even exaggerating for show. “This is so nice, Jimmy. Man, I wish you could feel it, too. This is almost better than having your cock stroke mine.”</p><p>Jimmy’s face fell, but his eyes were glued to where Castiel was thrusting in and out of Dean. He had his hands clenched into fists and seemed rigid. Castiel dialled up the vibrations a little more, and both he and Dean let out a loud moan at the sensation.</p><p>“Fuck. Seriously, I don’t even think I need you anymore, Jimmy. This is so much better.” Castiel babbled, because it really felt amazing. But when Jimmy stared at him, face ashen, he realized he’d gone a little too far. “C’mere,” he demanded, reaching out his free hand towards his brother. </p><p>As soon as Jimmy was within reach, Castiel pulled him into a deep, hungry kiss. He buried his hand in his hair to keep him close after he broke the kiss. “Didn’t mean it like that,” Castiel apologized. “I love you too much. We both do. You know that, right?”</p><p>Jimmy sniffed and tried to turn away, but Castiel held him steady, searching for eye contact. Eventually Jimmy returned it and nodded a bit. “I know,” he sighed. “God, you fucking suck so much.”</p><p>Castiel grinned and let go. “But you love me anyway.” He winked. “Now enjoy the show, while it lasts.” He considered ordering Jimmy on the bed with Dean to get a close-up view once more, but Jimmy would be way too tempted to rub himself against the sheets. And this was still about him not getting any contact.</p><p>Refocusing on Dean again, instead, Castiel sped up his thrusts. When he felt himself getting close, which was regrettably too soon because it really felt fucking amazing, he angled the vibrator to push straight against Dean’s prostate and then kept it there while Cas’ cock continued to piston. Which meant that on every stroke in, Dean was stuffed full.</p><p>Dean had started begging a while ago, but now his pleas got more desperate. “It’s ok, Dean,” Castiel assured him. “Come whenever you want.” </p><p>Permission given, it only took one more thrust until Dean yelled and clenched around him as he came for the second time. Castiel stilled, turning the vibrator up a notch instead of down. He kept it in until Dean’s shudders got too strong and his legs gave out once more. Dean’s whole body just melted into the sheets.</p><p>Castiel smiled, happy to be able to give this to Dean. Then he turned the vibrator off and slid it out. Dean grunted, not moving an inch. When Castiel gathered him up again for a better angle, Dean cursed into the pillow. Smile turning into a feral grin, Castiel hammered into Dean until he reached his own climax.</p><p>As soon as Castiel came, Dean clenched around him once more and yelled out. Castiel had to bite his lip to keep his own noises down, enjoying the way Dean’s hole spasmed around him, milking him until his own legs were threatening to give out, as well. He pulled out and slumped face-first onto the bed next to Dean.</p><p>Dean nudged at him. “Making a mess all over the sheets,” he complained. “Gross.” But neither of them really moved.</p><p>“I could make Jimmy lick it off,” Castiel pondered, and Dean chuckled.</p><p>“Only if you want him to murder you in your sleep,” Dean mumbled in reply and scooted over to claim a kiss.</p><p>“I’m still right here, you fuckers,” Jimmy grumbled. But when Castiel rolled far enough over to raise an eyebrow at him, Jimmy rolled his eyes. “I’m going to take a cold shower,” he announced. “And when I’m done, I’m even bringing you a washcloth. Even if neither of you deserve it.”</p><p>He turned to leave for the bathroom and Castiel reared up. “Oh, Jimmy?”</p><p>“No touching myself, or you’ll know,” Jimmy finished for him, giving him the middle finger and leaving the room.</p><p>Castiel laughed and gathered Dean close, entwining their legs before he reached for the blanket to throw over them.</p><p>Dean sighed happily and burrowed closer. “How <i>do</i> you always know, though?” Dean asked, voice sounding half-asleep.</p><p>Castiel looked at him in surprise. He’d never asked before. Should he reveal his secret? He smirked. “You both have lousy poker faces. I can definitely see the guilt in yours.” He kissed Dean’s forehead. “And the smugness in Jimmy’s.”</p><p>Dean chuckled. “So if I learn to hide my guilt better, I can ignore your stupid demands and you won’t know?”</p><p>Castiel raised his eyebrow. “You want to rephrase that, love?”</p><p>“Thanks for being honest, Sir. I promise to always be honest with you?” Dean tried.</p><p>Castiel snorted but carded his hands through Dean’s hair lovingly, anyway. “You’re lucky I love you.”</p><p>“Love you, too,” Dean smiled and placed a kiss on Castiel’s chin. “And I’m sorry. Didn’t mean to mess with your work.”</p><p>“I know. But don’t assume I don’t also know that this whole little trick was your idea in the first place. You let Jimmy take the fall for you…” Castiel raised a finger when he saw Dean trying to protest. “And maybe Jimmy was even convinced it really was his idea, but I know better. I know <i>you</i>.”</p><p>Dean’s eyes gleamed and his face twitched, trying desperately to hide his grin, thus giving himself away. So open. That’s why Castiel always knew.</p><p>“And before you think you’ve gotten away with it, you’re gonna get your punishment tomorrow,” Castiel stated.</p><p>Dean pouted. “But you already punished me just now.”</p><p>“Oh, please.” Castiel gathered him a little closer. “Like any of this was a real punishment for you.”</p><p>Dean’s lips twitched and he gave up trying not to smile. “Fair,” he conceded. “Don’t tell Jimmy, though.”</p><p>“I don’t think his ego could take it.” Castiel grinned. It would only upset the balance between them if Jimmy realized both Cas and Dean knew how to play him. Besides, it would definitely ruin the fun if Jimmy became more suspicious of them.</p><p>Dean was almost asleep by the time Jimmy came back to bed, erection waned but not fully gone. Castiel pulled back the blanket and invited him to join them as a sign of peace. Jimmy took it and crawled in, pressing against Castiel’s free side and wrapping an arm around Dean.</p><p>As soon as they had all settled in together, Castiel made the announcement he’d been holding out for. </p><p>“We’re getting a cat.”</p><p>Both Dean and Jimmy looked up in surprise and then started to protest, but Castiel shushed them. “Just think about it. The shelters are currently overflowing and somewhere there’s a poor little ball of fluff just waiting for us.” He made his lip quiver a bit. “And we could definitely use some more joy right now, right? Just think about having a cat stroking up against your legs while you’re cooking, or cuddling up next to you on the sofa. Or having someone to play with while two of us are busy.”</p><p>They still didn’t seem too convinced, so Castiel decided to add a little guilt and mention his Zoom. He addressed Dean specifically. “Unless you want to dress up as my sex kitten and parade around my screen for my students next time…” Castiel trailed off when he noticed Jimmy’s raised eyebrows and Dean’s sudden flush. He groaned. Wrong tactic. “You would, wouldn’t you? Forgive me for forgetting about your exhibitionist kink for a second.” </p><p>Dean was fucking shameless. About all things sex-related, anyway. Sometimes Castiel misjudged quite how deep it ran. He ruffled Dean’s hair and gave him a quick peck on the lips. “How about this, instead? When we buy cat toys, we’ll also buy some for you and when the actual cat has settled in, Jimmy and I will train our other kitten?”</p><p>“We’re not getting <i>two</i> cats, for fuck’s sake, Cas.” Jimmy protested and Castiel smacked him upside his head. “Oh,” Jimmy realized, too late.</p><p>Dean was squirming, clearly conflicted, and Castiel cupped his cheek. “Dean. If your allergies come back, of course we’ll rehome the cat.” He had been fine after their friend Charlie had gotten a cat. In fact, Dean had only mentioned showing allergy symptoms once, back when he was a kid. Otherwise, Castiel wouldn’t even be suggesting this. He didn’t want Dean to suffer. From allergies, anyway. He still deserved a little more suffering for the stunt he’d pulled today, but that would be administered tomorrow. And did not actually involve getting a cat and ignoring his wishes.</p><p>Dean nodded, rubbing his cheek against Castiel’s fingers. “Can we still keep, uhm, <i>my</i> cat toys, even if the actual cat has to go?”</p><p>Castiel was a little surprised that Dean had stopped arguing so easily about getting a pet. Damn, he’d really hit a nerve with his suggestion, hadn’t he? Or maybe Dean was just still too much in his own space. “If you like them, sure.” He could see Jimmy open his mouth, but a sharp glare from Castiel shut him up. He would not ruin this for Dean with a bad joke. “But we’ll properly discuss this again tomorrow, when you’re not high on endorphins. Ok, sweetheart?”</p><p>Dean burrowed a little closer and reached behind him to pull Jimmy in. “Love you,” Dean mumbled and Castiel stroked his hair. Yeah. Dean was clearly out of it. Didn’t mean he hadn’t technically agreed to getting the cat, though. Castiel smiled and kissed Dean’s forehead, then he turned towards Jimmy.</p><p>“Cat?” he asked.</p><p>Jimmy rolled his eyes. “I can’t believe this ended with you punishing me <i>and</i> getting a pet. How do you always do this, Cas?”</p><p>Castiel smiled brightly. “It’s because you love me and generally want me to be happy.”</p><p>Jimmy groaned. “Yeah. Save that sappy shit for Dean, over there.”</p><p>Dean was still awake enough to hold up his middle finger for Jimmy, and Castiel’s smile only grew. He really was the luckiest. He leaned over and claimed a kiss from Jimmy, then settled in for sleep, cocooned between the two men he loved. </p><p>They still needed to have a proper talk tomorrow, but for now they were definitely forgiven. After all, the whole fiasco was finally getting him a cat.</p>
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